CA1339835C - Luminescent metal chelate labels and meand for detection - Google Patents
Luminescent metal chelate labels and meand for detectionInfo
- Publication number
- CA1339835C CA1339835C CA000494077A CA494077A CA1339835C CA 1339835 C CA1339835 C CA 1339835C CA 000494077 A CA000494077 A CA 000494077A CA 494077 A CA494077 A CA 494077A CA 1339835 C CA1339835 C CA 1339835C
- Authority
- CA
- Canada
- Prior art keywords
- chemical moiety
- chemical
- electromagnetic radiation
- substituted
- moiety
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000001514 detection method Methods 0.000 title claims description 13
- 229910052751 metal Inorganic materials 0.000 title description 11
- 239000002184 metal Substances 0.000 title description 10
- 239000013522 chelant Substances 0.000 title 1
- 239000000126 substance Substances 0.000 claims abstract description 298
- 238000000034 method Methods 0.000 claims abstract description 197
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 69
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 65
- -1 biochemical Substances 0.000 claims abstract description 55
- 229910052762 osmium Inorganic materials 0.000 claims abstract description 40
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 239000003446 ligand Substances 0.000 claims description 102
- 230000005670 electromagnetic radiation Effects 0.000 claims description 95
- 239000000203 mixture Substances 0.000 claims description 79
- 239000012491 analyte Substances 0.000 claims description 54
- 239000003153 chemical reaction reagent Substances 0.000 claims description 53
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 48
- 239000000463 material Substances 0.000 claims description 47
- 230000027455 binding Effects 0.000 claims description 25
- 238000009739 binding Methods 0.000 claims description 25
- 230000001939 inductive effect Effects 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 19
- 150000001408 amides Chemical class 0.000 claims description 18
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 17
- 108020004707 nucleic acids Proteins 0.000 claims description 15
- 150000007523 nucleic acids Chemical class 0.000 claims description 15
- 102000039446 nucleic acids Human genes 0.000 claims description 15
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 15
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 15
- 229920001184 polypeptide Polymers 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 239000002245 particle Substances 0.000 claims description 13
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
- 239000005556 hormone Substances 0.000 claims description 12
- 229940088597 hormone Drugs 0.000 claims description 12
- 239000002207 metabolite Substances 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 12
- 210000002966 serum Anatomy 0.000 claims description 12
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 11
- 102000004169 proteins and genes Human genes 0.000 claims description 11
- 108090000623 proteins and genes Proteins 0.000 claims description 11
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- 229930013930 alkaloid Natural products 0.000 claims description 10
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- 125000001931 aliphatic group Chemical group 0.000 claims description 9
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- 235000000346 sugar Nutrition 0.000 claims description 9
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims description 8
- 150000007945 N-acyl ureas Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001409 amidines Chemical class 0.000 claims description 8
- 150000003857 carboxamides Chemical class 0.000 claims description 8
- 150000007942 carboxylates Chemical class 0.000 claims description 8
- 239000013043 chemical agent Substances 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 7
- 238000010521 absorption reaction Methods 0.000 claims description 7
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims description 7
- 238000003556 assay Methods 0.000 claims description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 7
- 150000002527 isonitriles Chemical class 0.000 claims description 7
- 150000002825 nitriles Chemical class 0.000 claims description 7
- 229920001282 polysaccharide Polymers 0.000 claims description 7
- 230000009467 reduction Effects 0.000 claims description 7
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical class [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
- 230000009137 competitive binding Effects 0.000 claims description 6
- 229920006008 lipopolysaccharide Polymers 0.000 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 6
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 5
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 5
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 229940095064 tartrate Drugs 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 230000001186 cumulative effect Effects 0.000 claims description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 4
- AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 239000005495 thyroid hormone Substances 0.000 claims description 3
- 229940036555 thyroid hormone Drugs 0.000 claims description 3
- WDJUZGPOPHTGOT-OAXVISGBSA-N Digitoxin Natural products O([C@H]1[C@@H](C)O[C@@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@@](C)([C@H](C6=CC(=O)OC6)CC5)CC4)CC3)CC2)C[C@H]1O)[C@H]1O[C@@H](C)[C@H](O[C@H]2O[C@@H](C)[C@@H](O)[C@@H](O)C2)[C@@H](O)C1 WDJUZGPOPHTGOT-OAXVISGBSA-N 0.000 claims description 2
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 claims description 2
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- 241000244206 Nematoda Species 0.000 claims description 2
- 239000013060 biological fluid Substances 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
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- WDJUZGPOPHTGOT-XUDUSOBPSA-N digitoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O WDJUZGPOPHTGOT-XUDUSOBPSA-N 0.000 claims description 2
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- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 claims description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/002—Osmium compounds
- C07F15/0026—Osmium compounds without a metal-carbon linkage
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/533—Production of labelled immunochemicals with fluorescent label
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/805—Optical property
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/806—Electrical property or magnetic property
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Pathology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Materials By Optical Means (AREA)
- Pyridine Compounds (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66698784A | 1984-10-31 | 1984-10-31 | |
| US666,987 | 1985-10-24 | ||
| US06/789,113 US5238808A (en) | 1984-10-31 | 1985-10-24 | Luminescent metal chelate labels and means for detection |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1339835C true CA1339835C (en) | 1998-04-21 |
Family
ID=27099589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000494077A Expired - Lifetime CA1339835C (en) | 1984-10-31 | 1985-10-29 | Luminescent metal chelate labels and meand for detection |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5238808A (xx) |
| EP (2) | EP0199804B1 (xx) |
| JP (4) | JPH0826054B2 (xx) |
| AT (2) | ATE230114T1 (xx) |
| AU (1) | AU5020085A (xx) |
| CA (1) | CA1339835C (xx) |
| DE (2) | DE3587793T2 (xx) |
| HK (2) | HK1007349A1 (xx) |
| IL (1) | IL76872A (xx) |
| WO (1) | WO1986002734A1 (xx) |
Families Citing this family (224)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK365785A (da) * | 1984-09-17 | 1986-03-18 | Hoffmann La Roche | Metalcomplexer |
| US5238808A (en) * | 1984-10-31 | 1993-08-24 | Igen, Inc. | Luminescent metal chelate labels and means for detection |
| US5310687A (en) * | 1984-10-31 | 1994-05-10 | Igen, Inc. | Luminescent metal chelate labels and means for detection |
| US5585279A (en) * | 1986-01-23 | 1996-12-17 | Davidson; Robert S. | Time-resolved luminescence binding assays using a fluorescent transition metal label other than ruthenium |
| GB8601646D0 (en) * | 1986-01-23 | 1986-02-26 | Davidson R S | Binding assay & reagent |
| US4732974A (en) * | 1986-03-05 | 1988-03-22 | Mallinckrodt, Inc. | Metal ion labeling of carrier molecules |
| US5591581A (en) * | 1986-04-30 | 1997-01-07 | Igen, Inc. | Electrochemiluminescent rhenium moieties and methods for their use |
| US6316607B1 (en) | 1986-04-30 | 2001-11-13 | Igen International, Inc. | Electrochemiluminescent assays |
| US6165729A (en) * | 1986-04-30 | 2000-12-26 | Hyperion Catalysis International, Inc. | Electrochemiluminescent reaction utilizing amine-derived reductant |
| US6881536B1 (en) * | 1986-04-30 | 2005-04-19 | Bioveris Corporation | Particle based electrochemiluminescent assays |
| EP0265519B1 (en) * | 1986-04-30 | 1995-09-13 | IGEN, INC. (a California corporation) | Electrochemiluminescent assays |
| US5770459A (en) * | 1986-04-30 | 1998-06-23 | Igen International, Inc. | Methods and apparatus for improved luminescence assays using particle concentration, electrochemical generation of chemiluminescence detection |
| US6451225B1 (en) * | 1986-04-30 | 2002-09-17 | Igen International, Inc. | Electrochemiluminescent reaction utilizing amine-derived reductant |
| US6271041B1 (en) * | 1986-04-30 | 2001-08-07 | Igen International, Inc. | Electrochemiluminescent reaction utilizing amine-derived reductant |
| US5714380A (en) | 1986-10-23 | 1998-02-03 | Amoco Corporation | Closed vessel for isolating target molecules and for performing amplification |
| US4855930A (en) * | 1987-03-27 | 1989-08-08 | Chimerix Corporation | Method and appartatus for improved time-resolved fluorescence spectroscopy |
| WO1988007670A2 (en) * | 1987-03-27 | 1988-10-06 | Chimerix Corporation | Time-resolved fluorescence apparatus and immunoassay |
| US6881589B1 (en) * | 1987-04-30 | 2005-04-19 | Bioveris Corporation | Electrochemiluminescent localizable complexes for assay compositions |
| US5935779A (en) * | 1988-11-03 | 1999-08-10 | Igen International Inc. | Methods for improved particle electrochemiluminescence assay |
| HU204856B (en) * | 1987-08-12 | 1992-02-28 | Orszagos Mueszaki Fejlesztesi | Process for releasing cell mixtures and tissues from undesired populations and for producing monoclonal antibody - hematoporphyrin conjugates |
| ATE259064T1 (de) * | 1987-11-04 | 2004-02-15 | Igen Int Inc | Lumineszente rhenium-komplexe und verfahren zur herstellung |
| SE8800613D0 (sv) * | 1988-02-23 | 1988-02-23 | Wallac Oy | A novel spectrofluorometric method and compounds that are of value for the method |
| SE461117B (sv) * | 1988-03-21 | 1990-01-08 | Jouko J Kankare | Foerfarande foer bestaemning av koncentrationen av en luminiscerande lantanid foerening |
| US5308754A (en) * | 1988-03-21 | 1994-05-03 | Kankare Jouko J | Electrogenerated luminescence in solution |
| US5093268A (en) * | 1988-04-28 | 1992-03-03 | Igen, Inc. | Apparatus for conducting a plurality of simultaneous measurements of electrochemiluminescent phenomena |
| CA1325527C (en) * | 1988-04-28 | 1993-12-28 | Nicholas Leventis | Apparatus for conducting a plurality of simultaneous measurements of electrochemiluminescent phenomena |
| US6702986B1 (en) | 1988-04-29 | 2004-03-09 | Igen International, Inc. | Electrochemiluminescent reaction utilizing amine-derived reductant |
| CA2002083C (en) * | 1988-11-03 | 2001-01-09 | Haresh P. Shah | Enhanced electrochemiluminescence |
| US5068088A (en) * | 1988-11-03 | 1991-11-26 | Igen, Inc. | Method and apparatus for conducting electrochemiluminescent measurements |
| US5247243A (en) * | 1988-11-03 | 1993-09-21 | Igen, Inc. | Method and apparatus for conducting electrochemiluminescent measurements |
| US5061445A (en) * | 1988-11-03 | 1991-10-29 | Igen, Inc. | Apparatus for conducting measurements of electrochemiluminescent phenomena |
| JPH076913B2 (ja) * | 1988-11-03 | 1995-01-30 | イゲン，インコーポレーテッド | アミン誘導還元剤を利用する電気化学発光反応 |
| US5298427A (en) * | 1990-04-24 | 1994-03-29 | The Board Of Trustees Of The University Of Arkansas | Chemiluminescent detection of amino acids |
| IL100866A (en) * | 1991-02-06 | 1995-10-31 | Igen Inc | Luminescence test method and device based on magnetic tiny particles, containing many magnets |
| ZA92804B (en) | 1991-02-06 | 1992-12-30 | Igen Inc | Methods and apparatus for improved luminescence assays |
| FR2673183B1 (fr) * | 1991-02-21 | 1996-09-27 | Asulab Sa | Complexes mono, bis ou tris (2,2'-bipyridine substituee) d'un metal choisi parmi le fer, le ruthenium, l'osmium ou le vanadium et leurs procedes de preparation . |
| KR100212178B1 (ko) * | 1991-07-10 | 1999-08-02 | 리차드 제이 마세이 | 입자농도 및 화학발광 검출을 이용한 개선된 발광 검정 장치 및 방법 |
| ZA929351B (en) * | 1991-12-11 | 1993-06-04 | Igen Inc | Electrochemiluminescent label for DNA assays. |
| US5541113A (en) * | 1993-09-22 | 1996-07-30 | Beckman Instruments, Inc. | Method for detecting an analyte using an electrochemical luminescent transition metal label |
| US6071699A (en) | 1996-06-07 | 2000-06-06 | California Institute Of Technology | Nucleic acid mediated electron transfer |
| US5591578A (en) * | 1993-12-10 | 1997-01-07 | California Institute Of Technology | Nucleic acid mediated electron transfer |
| AU690315B2 (en) * | 1994-07-25 | 1998-04-23 | Boehringer Mannheim Gmbh | Metal complexes with charged linker |
| WO1996003651A1 (de) | 1994-07-25 | 1996-02-08 | Boehringer Mannheim Gmbh | Metallchelat-markierte peptide |
| JP3583436B2 (ja) * | 1994-07-25 | 2004-11-04 | ロシュ ダイアグノスティックス ゲーエムベーハー | 親水性金属錯体 |
| US5786141A (en) * | 1994-08-26 | 1998-07-28 | Bard; Allen J. | Electrogenerated chemiluminescence labels for analysis and/or referencing |
| AU703344B2 (en) * | 1994-08-26 | 1999-03-25 | Igen International, Inc. | Biosensor for and method of electrogenerated chemiluminescent detection of nucleic acid adsorbed to a solid surface |
| US5620850A (en) * | 1994-09-26 | 1997-04-15 | President And Fellows Of Harvard College | Molecular recognition at surfaces derivatized with self-assembled monolayers |
| US6472148B1 (en) | 1994-09-26 | 2002-10-29 | President And Fellows Of Harvard College | Molecular recognition at surfaces derivatized with self-assembled monolayers |
| US5744367A (en) * | 1994-11-10 | 1998-04-28 | Igen International, Inc. | Magnetic particle based electrochemiluminescent detection apparatus and method |
| FR2727415A1 (fr) * | 1994-11-30 | 1996-05-31 | Commissariat Energie Atomique | Complexes du ruthenium utilisables en particulier pour determiner la topologie des proteines, et leur procede de preparation |
| US20010003647A1 (en) * | 1995-06-07 | 2001-06-14 | Ji Sun | Coreatant-including electrochemiluminescent compounds, methods, systems and kits utilizing same |
| US5610075A (en) * | 1995-01-17 | 1997-03-11 | Stahl-Rees; Marianne | Competitive electrochemiluminescence assays for endotoxins using a ruthenium label |
| US6673533B1 (en) * | 1995-03-10 | 2004-01-06 | Meso Scale Technologies, Llc. | Multi-array multi-specific electrochemiluminescence testing |
| US6207369B1 (en) | 1995-03-10 | 2001-03-27 | Meso Scale Technologies, Llc | Multi-array, multi-specific electrochemiluminescence testing |
| US6140045A (en) | 1995-03-10 | 2000-10-31 | Meso Scale Technologies | Multi-array, multi-specific electrochemiluminescence testing |
| CZ299135B6 (cs) | 1995-03-10 | 2008-04-30 | Meso Scale Technologies, Llc. Corporation Servicecompany | Kazeta a zarízení pro použití pri detekci analytu, zpusob provádení testu za použití uvedené kazety, kit pro použití pri provádení množiny elektrochemiluminescencních testu a zpusob detekce nebo merení analytu |
| WO1996033411A1 (en) * | 1995-04-18 | 1996-10-24 | Igen, Inc. | Electrochemiluminescence of rare earth metal chelates |
| US6319670B1 (en) | 1995-05-09 | 2001-11-20 | Meso Scale Technology Llp | Methods and apparatus for improved luminescence assays using microparticles |
| AU5920696A (en) * | 1995-05-18 | 1996-11-29 | Igen, Inc. | Method for derivitizing electrodes and assay methods using s uch derivitized electrodes |
| WO1996041175A1 (en) | 1995-06-07 | 1996-12-19 | Igen, Inc. | Electrochemiluminescent enzyme immunoassay |
| US5807978A (en) | 1995-06-07 | 1998-09-15 | Kokolus; William J. | Immunogenic peptides of prostate specific antigen |
| US6099760A (en) * | 1995-06-07 | 2000-08-08 | Igen, Inc. | Hydrogen peroxide based ECL |
| JP3574457B2 (ja) * | 1995-09-12 | 2004-10-06 | エーザイ株式会社 | 電気化学発光検出方法と装置 |
| FR2747694B1 (fr) * | 1996-04-18 | 1998-06-05 | France Etat | Cathode pour la reduction de dioxyde de carbone et procede de fabrication d'une telle cathode |
| US20030078416A1 (en) * | 1996-04-30 | 2003-04-24 | Yitzhak Tor | Substituted phenanthrolines |
| CA2259493A1 (en) * | 1996-07-03 | 1998-01-08 | President And Fellows Of Harvard College | Oligonucleotide linker and techniques involving immobilized and linked oligonucleotides |
| US7381525B1 (en) * | 1997-03-07 | 2008-06-03 | Clinical Micro Sensors, Inc. | AC/DC voltage apparatus for detection of nucleic acids |
| US7014992B1 (en) * | 1996-11-05 | 2006-03-21 | Clinical Micro Sensors, Inc. | Conductive oligomers attached to electrodes and nucleoside analogs |
| US6096273A (en) * | 1996-11-05 | 2000-08-01 | Clinical Micro Sensors | Electrodes linked via conductive oligomers to nucleic acids |
| US7045285B1 (en) * | 1996-11-05 | 2006-05-16 | Clinical Micro Sensors, Inc. | Electronic transfer moieties attached to peptide nucleic acids |
| US5958573A (en) * | 1997-02-10 | 1999-09-28 | Quantum Energy Technologies | Electroluminescent device having a structured particle electron conductor |
| US5976887A (en) * | 1997-06-02 | 1999-11-02 | Applied Research Associates, Inc. | Electrochemiluminescence assays based on interactions with soluble metal ions and diaminoaromatic ligands |
| US6013459A (en) | 1997-06-12 | 2000-01-11 | Clinical Micro Sensors, Inc. | Detection of analytes using reorganization energy |
| US6613583B1 (en) | 1997-06-27 | 2003-09-02 | Igen International, Inc. | Electrochemiluminescent label based on multimetallic assemblies |
| US7745142B2 (en) | 1997-09-15 | 2010-06-29 | Molecular Devices Corporation | Molecular modification assays |
| DE19811582A1 (de) | 1998-03-17 | 1999-09-23 | Roche Diagnostics Gmbh | Stabilisierung und Verstärkung von Elektrochemilumineszenz-Signalen |
| ATE221657T1 (de) | 1998-05-06 | 2002-08-15 | Roche Diagnostics Gmbh | Entstörung durch rheumafaktoren |
| US6200531B1 (en) | 1998-05-11 | 2001-03-13 | Igen International, Inc. | Apparatus for carrying out electrochemiluminescence test measurements |
| AU761879B2 (en) | 1998-05-19 | 2003-06-12 | Research Development Foundation | Triterpene compositions and methods for use thereof |
| WO1999063346A1 (en) | 1998-06-01 | 1999-12-09 | Roche Diagnostics Corporation | Method and device for electrochemical immunoassay of multiple analytes |
| US7087148B1 (en) | 1998-06-23 | 2006-08-08 | Clinical Micro Sensors, Inc. | Binding acceleration techniques for the detection of analytes |
| DE19828441A1 (de) * | 1998-06-25 | 1999-12-30 | Roche Diagnostics Gmbh | Verwendung derivatisierter Reagenzien in Chemilumineszenz- und Elektrochemilumineszenz-Nachweisverfahren |
| WO2000001848A1 (fr) * | 1998-07-01 | 2000-01-13 | Hitachi, Ltd. | Appareil et methode de criblage de polynucleotide |
| EP1131633A2 (en) | 1998-11-16 | 2001-09-12 | Board of Regents, The University of Texas System | Hiv-specific t-cell induction |
| US6833267B1 (en) * | 1998-12-30 | 2004-12-21 | Clinical Micro Sensors, Inc. | Tissue collection devices containing biosensors |
| US20030068635A1 (en) * | 1999-02-16 | 2003-04-10 | Boehringer Mannheim Gmbh | Determination of an analyte using two labels |
| US7312087B2 (en) * | 2000-01-11 | 2007-12-25 | Clinical Micro Sensors, Inc. | Devices and methods for biochip multiplexing |
| US20020177135A1 (en) * | 1999-07-27 | 2002-11-28 | Doung Hau H. | Devices and methods for biochip multiplexing |
| DE19933104A1 (de) * | 1999-07-15 | 2001-01-18 | Ingo Klimant | Phosphoreszierende Mikro- und Nanopartikel als Referenzstandard und Phosphoreszenzmarker |
| CA2380258C (en) | 1999-07-26 | 2008-07-15 | Clinical Micro Sensors, Inc. | Sequence determination of nucleic acids using electronic detection |
| US6136268A (en) * | 1999-08-17 | 2000-10-24 | Orion Diagnostica | Method for luminescence measurements |
| US7141436B2 (en) * | 1999-11-03 | 2006-11-28 | Science And Technology Corp. | Immunoassay and reagents and kits for performing the same |
| CN1840607B (zh) * | 1999-12-01 | 2010-06-09 | 普林斯顿大学理事会 | 作为有机发光器件的磷光掺杂剂的l2mx形式的络合物 |
| US6824669B1 (en) | 2000-02-17 | 2004-11-30 | Motorola, Inc. | Protein and peptide sensors using electrical detection methods |
| WO2001094951A2 (en) * | 2000-06-08 | 2001-12-13 | Board Of Regents, The University Of Texas System | Inhibitors of c-reactive protein induced inflammation |
| AU2001277066A1 (en) * | 2000-07-21 | 2002-02-05 | University Of Maryland, Baltimore | Long wavelength long lifetime luminophores |
| US20060148732A1 (en) * | 2000-11-17 | 2006-07-06 | Gutterman Jordan U | Inhibition of NF-kappaB by triterpene compositions |
| GB0103765D0 (en) * | 2001-02-15 | 2001-04-04 | Affitech As | Assay |
| US20020173042A1 (en) * | 2001-03-16 | 2002-11-21 | Timothy Oolman | Method of tagging agricultural products |
| US6989276B2 (en) | 2001-05-10 | 2006-01-24 | Battelle Energy Alliance, Llc | Rapid classification of biological components |
| USRE44031E1 (en) | 2001-05-10 | 2013-02-26 | Battelle Energy Alliance, Llc | Antibody profiling sensitivity through increased reporter antibody layering |
| USRE46351E1 (en) | 2001-05-10 | 2017-03-28 | Battelle Energy Alliance, Llc | Antibody profiling sensitivity through increased reporter antibody layering |
| US7695919B2 (en) | 2001-05-10 | 2010-04-13 | Battelle Energy Alliance, Llc | Antibody profiling sensitivity through increased reporter antibody layering |
| SE0102327D0 (sv) | 2001-06-28 | 2001-06-28 | Active Biotech Ab | A novel engineered superantigen for human therapy |
| EP2420824B1 (en) | 2001-06-29 | 2018-11-28 | Meso Scale Technologies LLC | Multi-well plate having an array of wells and kit for use in the conduct of an ECL assay |
| US8815577B2 (en) | 2001-07-30 | 2014-08-26 | Meso Scale Technologies, Llc | Assay electrode having immobilized lipid/protein layers, methods of making the same and methods of using the same for luminescence test measurements |
| KR100454868B1 (ko) * | 2001-08-01 | 2004-11-05 | 주식회사 아이센스 | 신규의 전기화학발광 면역분석 표지물질인 루테늄착화합물 및 그의 제조방법 |
| CA2459893C (en) * | 2001-09-10 | 2014-01-21 | Meso Scale Technologies, Llc | Methods and apparatus for conducting multiple measurements on a sample |
| US7553448B2 (en) | 2002-06-20 | 2009-06-30 | Bioveris Corporation | Electrochemiluminescence flow cell and flow cell components |
| AU2003270619A1 (en) * | 2002-09-12 | 2004-04-30 | Molecular Probes, Inc. | Site-specific labeling of affinity tags in fusion proteins |
| US7000870B2 (en) * | 2002-11-07 | 2006-02-21 | Aerion Corporation | Laminar flow wing for transonic cruise |
| US20050003422A1 (en) | 2003-07-01 | 2005-01-06 | Mitch Reponi | Methods for assessing and treating cancer |
| US7238536B1 (en) | 2004-03-22 | 2007-07-03 | Florida State University Research Foundation, Inc. | Controlled transport through multiple reversible interaction point membranes |
| US7514223B2 (en) * | 2004-05-15 | 2009-04-07 | Genentech, Inc. | Cross-screening system and methods for detecting a molecule having binding affinity for a target molecule |
| US20080227219A1 (en) * | 2004-11-17 | 2008-09-18 | Frank Gamez | Electrochemiluminescent assay |
| US20060275841A1 (en) * | 2004-12-20 | 2006-12-07 | Martin Blankfard | Assay method and apparatus with reduced sample matrix effects |
| EP3228624A3 (en) * | 2005-02-10 | 2017-11-01 | Yeda Research And Development Co., Ltd. | Redox-active chromophore molecules and devices utilizing the same |
| US8211279B2 (en) * | 2005-06-03 | 2012-07-03 | Board Of Regents Of The University Of Texas System | Electrochemistry and electrogenerated chemiluminescence with a single faradaic electrode |
| US20070116600A1 (en) * | 2005-06-23 | 2007-05-24 | Kochar Manish S | Detection device and methods associated therewith |
| US20070026012A1 (en) | 2005-08-01 | 2007-02-01 | Cornell Research Foundation, Inc. | Compositions and methods for monitoring and altering protein folding and solubility |
| CA2637598A1 (en) | 2006-01-18 | 2007-02-14 | University Of Chicago | Compositions and methods related to staphylococcal bacterium proteins |
| ES2498377T3 (es) | 2006-03-09 | 2014-09-24 | F. Hoffmann-La Roche Ag | Ensayo de anticuerpos antifármaco |
| US20080108513A1 (en) * | 2006-06-01 | 2008-05-08 | Northwestern University | Cellular Arrays |
| US7749772B1 (en) | 2006-06-29 | 2010-07-06 | Varian, Inc. | Antibody and immunoassays for determining the presence of Δ9-Tetrahydrocannabinol |
| EP2067044B1 (en) | 2006-09-12 | 2013-07-03 | F. Hoffmann-La Roche AG | Anti-drug antibody assay |
| AU2007351787A1 (en) * | 2006-10-20 | 2008-10-30 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Modified cyanobacteria |
| KR100869589B1 (ko) | 2006-12-19 | 2008-11-21 | 단국대학교 산학협력단 | 바이오센서를 이용한 생체 물질의 정량적 측정 방법 |
| US8951631B2 (en) | 2007-01-03 | 2015-02-10 | Applied Nanostructured Solutions, Llc | CNT-infused metal fiber materials and process therefor |
| US8158217B2 (en) | 2007-01-03 | 2012-04-17 | Applied Nanostructured Solutions, Llc | CNT-infused fiber and method therefor |
| US8951632B2 (en) | 2007-01-03 | 2015-02-10 | Applied Nanostructured Solutions, Llc | CNT-infused carbon fiber materials and process therefor |
| US9005755B2 (en) | 2007-01-03 | 2015-04-14 | Applied Nanostructured Solutions, Llc | CNS-infused carbon nanomaterials and process therefor |
| WO2008104344A1 (en) | 2007-02-27 | 2008-09-04 | F. Hoffmann-La Roche Ag | Method for the assessment of the inhibitory activity of antibodies against insulin-like growth factor i receptor |
| US20080300796A1 (en) | 2007-05-31 | 2008-12-04 | Lassahn Gordon D | Biological analysis methods, biological analysis devices, and articles of manufacture |
| GB0711849D0 (en) | 2007-06-19 | 2007-07-25 | Oxford Biosensors Ltd | Redox Mediators |
| AU2008337904B2 (en) | 2007-12-15 | 2014-02-13 | F. Hoffmann-La Roche Ag | Distinguishing assay |
| WO2009146043A1 (en) * | 2008-03-31 | 2009-12-03 | Cohen B Arial | Assay for semen optimization |
| US9383369B2 (en) | 2008-03-31 | 2016-07-05 | Barb Ariel Cohen | Methods for improving fertility and selectivity for desired offspring sex in artificial insemination |
| ES2457541T3 (es) | 2008-04-11 | 2014-04-28 | Board Of Regents Of The University Of Texas System | Método y aparato para la amplificación de la quimioluminiscencia electrogenerada por nanopartículas |
| CA2717454C (en) | 2008-05-08 | 2017-02-14 | Board Of Regents Of The University Of Texas System | Luminescent nanostructured materials for use in electrogenerated chemiluminescence |
| US8264347B2 (en) | 2008-06-24 | 2012-09-11 | Trelleborg Sealing Solutions Us, Inc. | Seal system in situ lifetime measurement |
| AU2009302582A1 (en) | 2008-10-06 | 2010-04-15 | University Of Chicago | Compositions and methods related to bacterial Eap, Emp, and/or AdsA proteins |
| US8614297B2 (en) | 2008-12-22 | 2013-12-24 | Hoffmann-La Roche Inc. | Anti-idiotype antibody against an antibody against the amyloid β peptide |
| CA2750484A1 (en) | 2009-02-17 | 2010-12-16 | Applied Nanostructured Solutions, Llc | Composites comprising carbon nanotubes on fiber |
| AU2010257117A1 (en) | 2009-02-27 | 2011-08-11 | Applied Nanostructured Solutions Llc | Low temperature CNT growth using gas-preheat method |
| US20100227134A1 (en) | 2009-03-03 | 2010-09-09 | Lockheed Martin Corporation | Method for the prevention of nanoparticle agglomeration at high temperatures |
| KR101773368B1 (ko) | 2009-04-03 | 2017-08-31 | 유니버시티 오브 시카고 | 단백질 Ａ(ＳｐＡ) 변이체와 관련된 조성물 및 방법 |
| US20100261292A1 (en) | 2009-04-10 | 2010-10-14 | Meso Scale Technologies, Llc | Methods for Conducting Assays |
| US9111658B2 (en) | 2009-04-24 | 2015-08-18 | Applied Nanostructured Solutions, Llc | CNS-shielded wires |
| JP2012525012A (ja) | 2009-04-24 | 2012-10-18 | アプライド ナノストラクチャード ソリューションズ リミテッド ライアビリティー カンパニー | Ｃｎｔ浸出ｅｍｉ遮蔽複合材料及びコーティング |
| US8664573B2 (en) | 2009-04-27 | 2014-03-04 | Applied Nanostructured Solutions, Llc | CNT-based resistive heating for deicing composite structures |
| WO2011017094A2 (en) | 2009-07-27 | 2011-02-10 | Ian Chamberlin | Assay apparatuses, consumables and methods |
| CN102470546B (zh) | 2009-08-03 | 2014-08-13 | 应用纳米结构方案公司 | 纳米颗粒在复合材料纤维中的结合 |
| US9410965B2 (en) | 2009-09-17 | 2016-08-09 | Battelle Energy Alliance, Llc | Identification of discriminant proteins through antibody profiling, methods and apparatus for identifying an individual |
| US8969009B2 (en) | 2009-09-17 | 2015-03-03 | Vicki S. Thompson | Identification of discriminant proteins through antibody profiling, methods and apparatus for identifying an individual |
| US8168291B2 (en) | 2009-11-23 | 2012-05-01 | Applied Nanostructured Solutions, Llc | Ceramic composite materials containing carbon nanotube-infused fiber materials and methods for production thereof |
| US8601965B2 (en) | 2009-11-23 | 2013-12-10 | Applied Nanostructured Solutions, Llc | CNT-tailored composite sea-based structures |
| JP2013520328A (ja) | 2009-12-14 | 2013-06-06 | アプライド ナノストラクチャード ソリューションズ リミテッド ライアビリティー カンパニー | カーボン・ナノチューブ浸出繊維材料を含んだ難燃性複合材料及び製品 |
| US9167736B2 (en) | 2010-01-15 | 2015-10-20 | Applied Nanostructured Solutions, Llc | CNT-infused fiber as a self shielding wire for enhanced power transmission line |
| CN102741465A (zh) | 2010-02-02 | 2012-10-17 | 应用纳米结构方案公司 | 包含平行排列的碳纳米管的碳纳米管并入的纤维材料、其制造方法及从其衍生的复合材料 |
| AU2011223738B2 (en) | 2010-03-02 | 2015-01-22 | Applied Nanostructured Solutions, Llc | Spiral wound electrical devices containing carbon nanotube-infused electrode materials and methods and apparatuses for production thereof |
| WO2011109485A1 (en) | 2010-03-02 | 2011-09-09 | Applied Nanostructured Solutions,Llc | Electrical devices containing carbon nanotube-infused fibers and methods for production thereof |
| JP2013523818A (ja) | 2010-04-05 | 2013-06-17 | ザ・ユニバーシティー・オブ・シカゴ | 免疫反応のエンハンサーとしてのプロテインＡ（ＳｐＡ）抗体に関連する組成物および方法 |
| US8780526B2 (en) | 2010-06-15 | 2014-07-15 | Applied Nanostructured Solutions, Llc | Electrical devices containing carbon nanotube-infused fibers and methods for production thereof |
| CN103037885B (zh) | 2010-07-02 | 2015-08-26 | 芝加哥大学 | 与蛋白A(SpA)变体相关的组合物和方法 |
| JP5805190B2 (ja) | 2010-08-19 | 2015-11-04 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 療法用モノクローナル抗体に結合する抗体の測定のためのアッセイ |
| US9017854B2 (en) | 2010-08-30 | 2015-04-28 | Applied Nanostructured Solutions, Llc | Structural energy storage assemblies and methods for production thereof |
| JP5793194B2 (ja) | 2010-09-09 | 2015-10-14 | ザ・ユニバーシティ・オブ・シカゴＴｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｃｈｉｃａｇｏ | 感染防御ブドウ球菌抗原が関与する方法および組成物 |
| BR112013005802A2 (pt) | 2010-09-14 | 2016-05-10 | Applied Nanostructured Sols | substratos de vidro com nanotubos de carbono crescidos sobre os mesmos e métodos para sua produção |
| CN104591123A (zh) | 2010-09-22 | 2015-05-06 | 应用奈米结构公司 | 具有碳纳米管成长于其上的碳纤维基板及其制造方法 |
| JP2014508370A (ja) | 2010-09-23 | 2014-04-03 | アプライド ナノストラクチャード ソリューションズ リミテッド ライアビリティー カンパニー | 強化送電線のセルフシールドワイヤとしてのｃｎｔ浸出繊維 |
| WO2012051386A2 (en) | 2010-10-14 | 2012-04-19 | Meso Scale Technologies, Llc | Reagent storage in an assay device |
| EP2712423A4 (en) | 2011-02-25 | 2015-06-10 | Wellstat Diagnostics Llc | ANALYZES FOR DETECTING ENZYMATIC ACTIVITY |
| WO2012143380A1 (en) | 2011-04-20 | 2012-10-26 | F. Hoffmann-La Roche Ag | Microwaves for immunohistochemical analysis |
| US8945588B2 (en) | 2011-05-06 | 2015-02-03 | The University Of Chicago | Methods and compositions involving protective staphylococcal antigens, such as EBH polypeptides |
| PE20141212A1 (es) | 2011-06-22 | 2014-09-19 | Hoffmann La Roche | Eliminacion de celulas diana por parte de celulas t citotoxicas especificas de virus utilizando complejos que comprenden mhc de clase 1 |
| JP6300727B2 (ja) | 2011-11-11 | 2018-03-28 | イーライ・エヌ・グレザー | コバインダー補助アッセイ法 |
| JP6203747B2 (ja) | 2011-12-19 | 2017-09-27 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 多特異性結合体の遊離結合パートナーの検出方法 |
| EP2620764B1 (en) | 2012-01-25 | 2015-11-04 | Roche Diagniostics GmbH | A luminescence method of detecting an analyte in a liquid sample and analysis system |
| CA2859268A1 (en) | 2012-02-01 | 2013-08-08 | F. Hoffmann-La Roche Ag | Method for the detection of a binding partner of a multispecific binder |
| US9085464B2 (en) | 2012-03-07 | 2015-07-21 | Applied Nanostructured Solutions, Llc | Resistance measurement system and method of using the same |
| EP2823310B1 (en) | 2012-03-08 | 2018-06-20 | F.Hoffmann-La Roche Ag | Multiplexed chromatography-immunoassay method for the characterization of circulating immune complexes |
| EP2844275B1 (en) | 2012-04-26 | 2020-05-13 | University of Chicago | Staphylococcal coagulase antigens and methods of their use |
| US9213043B2 (en) | 2012-05-15 | 2015-12-15 | Wellstat Diagnostics, Llc | Clinical diagnostic system including instrument and cartridge |
| US9081001B2 (en) | 2012-05-15 | 2015-07-14 | Wellstat Diagnostics, Llc | Diagnostic systems and instruments |
| US9625465B2 (en) | 2012-05-15 | 2017-04-18 | Defined Diagnostics, Llc | Clinical diagnostic systems |
| RU2636822C2 (ru) | 2012-07-13 | 2017-11-28 | Ф.Хоффманн-Ля Рош Аг | Способ обнаружения мультиспецифического связывающего агента |
| SG11201504414UA (en) | 2012-12-21 | 2015-07-30 | Hoffmann La Roche | Disulfide-linked multivalent mhc class i comprising multi-function proteins |
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| AU2014248759B2 (en) | 2013-03-13 | 2020-02-27 | Meso Scale Technologies, Llc. | Improved assay methods |
| US10202500B2 (en) | 2013-03-15 | 2019-02-12 | Lubrizol Advanced Materials, Inc. | Heavy metal free CPVC compounds |
| EP3404116B1 (en) | 2013-03-15 | 2022-10-19 | The University of Chicago | Methods and compositions related to t-cell activity |
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| IL229525A0 (en) | 2013-11-20 | 2014-01-30 | Yeda Res & Dev | Metal complexes of tris-bipyridyl and their uses in electrochromic applications |
| CA2947747C (en) | 2014-05-09 | 2024-03-05 | Meso Scale Technologies, Llc. | Graphene-modified electrodes |
| AU2015259048B2 (en) | 2014-05-15 | 2021-09-09 | Meso Scale Technologies, Llc. | Improved assay methods |
| IL295756A (en) | 2015-10-29 | 2022-10-01 | Hoffmann La Roche | Antibodies against fc-variable region and methods of use |
| CN108351361A (zh) | 2015-11-30 | 2018-07-31 | 豪夫迈·罗氏有限公司 | 用于测定Fc区修饰的抗体的免疫测定法 |
| CN108431231B (zh) * | 2016-01-29 | 2021-09-10 | 豪夫迈·罗氏有限公司 | 用于检测液体样本中的分析物的电化学发光方法和装置 |
| CN110892253A (zh) | 2017-08-01 | 2020-03-17 | 豪夫迈·罗氏有限公司 | 监测对液体样品中的分析物的检测操作的方法 |
| WO2019105916A1 (en) | 2017-11-29 | 2019-06-06 | F. Hoffmann-La Roche Ag | Target interference suppressed anti-drug antibody assay |
| US11686013B2 (en) | 2018-02-23 | 2023-06-27 | Meso Scale Technologies, Llc. | Methods of screening antigen-binding molecules by normalizing for the concentration of antigen-binding molecule |
| WO2019222708A2 (en) | 2018-05-17 | 2019-11-21 | Meso Scale Technologies, Llc. | Methods for isolating surface marker displaying agents |
| WO2020086751A1 (en) | 2018-10-23 | 2020-04-30 | Meso Scale Technologies, Llc. | Methods for isolating surface marker displaying agents |
| JP2022515543A (ja) | 2018-12-30 | 2022-02-18 | エフ．ホフマン－ラ ロシュ アーゲー | 抗ウサギｃｄ１９抗体および使用方法 |
| EP3906412A1 (en) | 2019-01-03 | 2021-11-10 | Meso Scale Technologies, LLC | Compositions and methods for carrying out assay measurements |
| AU2020232954A1 (en) | 2019-03-01 | 2021-09-09 | Meso Scale Technologies, Llc. | Electrochemiluminescent labeled probes for use in immunoassay methods, methods using such and kits comprising same |
| EP3969907A1 (en) | 2019-05-13 | 2022-03-23 | F. Hoffmann-La Roche AG | Interference-suppressed pharmacokinetic immunoassay |
| BR112021024624A2 (pt) | 2019-06-07 | 2022-01-18 | Hoffmann La Roche | Métodos para selecionar e fornecer um par de ligação de oligonucleotídeos de fita simples, para formar um duplex antiparalelo e para realizar um ensaio, par de ss-oligonucleotídeos complementares separados, duplex antiparalelo, uso de um par de ss-oligonucleotídeos separados, kit para realizar um ensaio e composição líquida |
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| EP4165409A1 (en) | 2020-06-16 | 2023-04-19 | F. Hoffmann-La Roche AG | Method for determining the free antigen of an antibody in a sample |
| AU2021299536A1 (en) | 2020-07-01 | 2023-02-16 | Meso Scale Technologies, Llc. | Compositions and methods for assay measurements |
| US20230349920A1 (en) | 2020-09-04 | 2023-11-02 | Meso Scale Technologies, Llc. | Methods for isolating central nervous system surface marker displaying agents |
| WO2022136234A1 (en) | 2020-12-22 | 2022-06-30 | F. Hoffmann-La Roche Ag | Method for detecting an analyte of interest in a sample |
| WO2022214565A1 (en) | 2021-04-09 | 2022-10-13 | F. Hoffmann-La Roche Ag | Process for selecting cell clones expressing a heterologous polypeptide |
| US20240210399A1 (en) | 2021-04-26 | 2024-06-27 | Meso Scale Technologies, Llc. | Methods for isolating and analyzing a target analyte encapsulated by a surface marker displaying agent |
| JP2024534067A (ja) | 2021-08-19 | 2024-09-18 | エフ． ホフマン－ラ ロシュ アーゲー | 多価抗バリアントｆｃ領域抗体および使用方法 |
| EP4416301A1 (en) | 2021-12-21 | 2024-08-21 | F. Hoffmann-La Roche AG | Method for the determination of hydrolytic activity |
| WO2023129884A1 (en) | 2021-12-30 | 2023-07-06 | Meso Scale Technologies, Llc. | Methods for electrochemiluminescence detection |
| CN118696234A (zh) | 2022-02-18 | 2024-09-24 | 豪夫迈·罗氏有限公司 | 用于检测样品中的目标分析物的方法 |
| WO2023212315A2 (en) | 2022-04-29 | 2023-11-02 | Meso Scale Technologies, Llc. | Methods for detecting and isolating extracellular vesicles |
| WO2024044622A1 (en) | 2022-08-24 | 2024-02-29 | Amgen Inc. | Anti-drug antibody assays |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3504052A (en) * | 1964-10-06 | 1970-03-31 | Mc Donnell Douglas Corp | Organometallic polymers |
| US3804869A (en) * | 1967-12-11 | 1974-04-16 | Rhone Poulenc Sa | Ruthenium complexes and processes for their preparation |
| US3530049A (en) * | 1968-10-02 | 1970-09-22 | Technic | Gold and ruthenium plating baths |
| GB1405592A (en) * | 1971-08-11 | 1975-09-10 | Johnson Matthey Co Ltd | Compounds of ruthenium |
| US3966556A (en) * | 1972-11-06 | 1976-06-29 | Syva Company | Compounds for enzyme amplification assay methadone analogs |
| DE2345412C2 (de) * | 1973-09-08 | 1983-11-03 | Bomag-Menck GmbH, 5407 Boppard | Zweiachsige Straßenwalze |
| US3996345A (en) * | 1974-08-12 | 1976-12-07 | Syva Company | Fluorescence quenching with immunological pairs in immunoassays |
| US4199559A (en) * | 1974-08-12 | 1980-04-22 | Syva Company | Fluorescence quenching with immunological pairs in immunoassays |
| US4058732A (en) * | 1975-06-30 | 1977-11-15 | Analytical Radiation Corporation | Method and apparatus for improved analytical fluorescent spectroscopy |
| IL49685A (en) * | 1976-05-31 | 1978-10-31 | Technion Res & Dev Foundation | Specific binding assay method for determining the concentration of materials and reagent means therefor |
| JPS6015957B2 (ja) * | 1976-09-08 | 1985-04-23 | 株式会社日立製作所 | 液晶マトリクス表示装置の駆動方法 |
| US4220722A (en) * | 1978-02-10 | 1980-09-02 | Syva Company | Method for conjugating to polyamino compounds employing haloacyl groups and compositions prepared thereby |
| US4277437A (en) * | 1978-04-05 | 1981-07-07 | Syva Company | Kit for carrying out chemically induced fluorescence immunoassay |
| US4363759A (en) * | 1978-04-10 | 1982-12-14 | Miles Laboratories, Inc. | Chemiluminescent-labeled haptens and antigens |
| US4238395A (en) * | 1978-07-24 | 1980-12-09 | Miles Laboratories, Inc. | Dimethyl 7-[ω-N-(phthalimido)alkyl]aminonaphthalene-1,2-dicarboxylates |
| US4238195A (en) * | 1979-01-18 | 1980-12-09 | Miles Laboratories, Inc. | Fluorescer-labeled specific binding assays |
| SE428332B (sv) * | 1979-03-08 | 1983-06-20 | Wallac Oy | Forfarande for fluorescensspektroskopisk bestemning av biologiskt aktivt emne, sasom hapten, antikropp eller antigen |
| US4432907A (en) * | 1979-09-10 | 1984-02-21 | Analytical Radiation Corporation | Diamine acid fluorescent chelates |
| US4352751A (en) * | 1979-09-10 | 1982-10-05 | Analytical Radiation Corporation | Species-linked diamine triacetic acids and their chelates |
| WO1981001883A1 (en) * | 1979-12-19 | 1981-07-09 | Electro Nucleonics | Chemical luminescence amplification substrate system for immunochemistry |
| US4293310A (en) * | 1980-03-14 | 1981-10-06 | University Of Pittsburgh | Photoelectrochemical immunoassay |
| CA1205028A (en) * | 1981-07-01 | 1986-05-27 | Jerald C. Hinshaw | Fluorescent chelates and labeled specific binding reagents prepared therefrom |
| US4637988A (en) * | 1981-07-01 | 1987-01-20 | Eastman Kodak Company | Fluorescent labels for immunoassay |
| US4707454A (en) * | 1981-08-10 | 1987-11-17 | Bio-Diagnostics, Inc. | Fluorescent chlorophyll labeled assay reagents |
| GB2112779B (en) * | 1981-12-11 | 1986-10-15 | Welsh Nat School Med | Aryl acridinium esters as luminescent labelling materials |
| US4707352A (en) * | 1984-01-30 | 1987-11-17 | Enzo Biochem, Inc. | Method of radioactively labeling diagnostic and therapeutic agents containing a chelating group |
| US4943523A (en) * | 1984-01-30 | 1990-07-24 | Enzo Biochem, Inc. | Detectable molecules, method of preparation and use |
| US4687747A (en) * | 1984-07-02 | 1987-08-18 | Mallinckrodt, Inc. | Phenanthridinium ester as a labelling compound in luminometric immunoassay |
| DK365785A (da) * | 1984-09-17 | 1986-03-18 | Hoffmann La Roche | Metalcomplexer |
| US5238808A (en) * | 1984-10-31 | 1993-08-24 | Igen, Inc. | Luminescent metal chelate labels and means for detection |
| US4699978A (en) * | 1985-01-18 | 1987-10-13 | The Trustees Of Columbia University In The City Of New York | Site-specific chiral ruthenium (II) and cobalt (III) antitumor agents |
| US4721669A (en) * | 1985-01-18 | 1988-01-26 | The Trustees Of Columbia University In The City Of New York | Chemical probes for left-handed DNA and chiral metal complexes as Z-specific anti-tumor agents |
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1985
- 1985-10-24 US US06/789,113 patent/US5238808A/en not_active Expired - Lifetime
- 1985-10-29 IL IL7687285A patent/IL76872A/xx not_active IP Right Cessation
- 1985-10-29 CA CA000494077A patent/CA1339835C/en not_active Expired - Lifetime
- 1985-10-30 AU AU50200/85A patent/AU5020085A/en not_active Abandoned
- 1985-10-30 EP EP85905702A patent/EP0199804B1/en not_active Expired - Lifetime
- 1985-10-30 JP JP60505060A patent/JPH0826054B2/ja not_active Expired - Lifetime
- 1985-10-30 EP EP93108292A patent/EP0580979B1/en not_active Expired - Lifetime
- 1985-10-30 DE DE3587793T patent/DE3587793T2/de not_active Expired - Lifetime
- 1985-10-30 AT AT93108292T patent/ATE230114T1/de not_active IP Right Cessation
- 1985-10-30 WO PCT/US1985/002153 patent/WO1986002734A1/en active IP Right Grant
- 1985-10-30 DE DE3588243T patent/DE3588243T2/de not_active Expired - Lifetime
- 1985-10-30 AT AT85905702T patent/ATE104057T1/de not_active IP Right Cessation
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1992
- 1992-11-19 JP JP4351891A patent/JP2710534B2/ja not_active Expired - Lifetime
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1994
- 1994-09-29 JP JP6235511A patent/JP2702075B2/ja not_active Expired - Lifetime
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1996
- 1996-07-24 JP JP8194842A patent/JP2706650B2/ja not_active Expired - Lifetime
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1998
- 1998-06-24 HK HK98106427A patent/HK1007349A1/xx not_active IP Right Cessation
- 1998-12-23 HK HK98115088A patent/HK1013861A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3587793T2 (de) | 1994-08-18 |
| JPS62500663A (ja) | 1987-03-19 |
| EP0199804B1 (en) | 1994-04-06 |
| DE3587793D1 (de) | 1994-05-11 |
| WO1986002734A1 (en) | 1986-05-09 |
| DE3588243D1 (de) | 2003-01-30 |
| IL76872A0 (en) | 1986-02-28 |
| EP0199804A1 (en) | 1986-11-05 |
| JP2710534B2 (ja) | 1998-02-10 |
| IL76872A (en) | 2000-12-06 |
| JP2706650B2 (ja) | 1998-01-28 |
| HK1013861A1 (en) | 1999-09-10 |
| JPH0665271A (ja) | 1994-03-08 |
| JPH0826054B2 (ja) | 1996-03-13 |
| EP0580979A3 (xx) | 1994-02-16 |
| JPH07173185A (ja) | 1995-07-11 |
| EP0580979A2 (en) | 1994-02-02 |
| DE3588243T2 (de) | 2003-10-30 |
| ATE230114T1 (de) | 2003-01-15 |
| EP0580979B1 (en) | 2002-12-18 |
| EP0199804A4 (en) | 1988-02-16 |
| JP2702075B2 (ja) | 1998-01-21 |
| JPH09110890A (ja) | 1997-04-28 |
| US5238808A (en) | 1993-08-24 |
| ATE104057T1 (de) | 1994-04-15 |
| AU5020085A (en) | 1986-05-15 |
| HK1007349A1 (en) | 1999-04-09 |
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